


All My Firsts

by spnsecret



Category: Supernatural
Genre: F/M, First Time, Minor Character Death
Language: English
Status: Completed
Published: 2014-11-02
Updated: 2014-11-02
Packaged: 2018-02-23 14:50:30
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,006
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2551544
Author URL: https://archiveofourown.org/users/spnsecret/pseuds/spnsecret
Summary: <blockquote class="userstuff">
              <p>Prompt: "can i have a dean oneshot where he is the readers first boyfriend. she's extremely self-conscious and hasn't even kissed anyone and has a lot of trust issues and a hard time getting close to people. dean takes things slow and when she wants sex she is terrified but dean makes sure she is ok and at the end he tells her he loves her."</p>
            </blockquote>





	All My Firsts

**Author's Note:**

> This turned out to have a bit more plot than I was expecting, but here it is. :)

The first time you met Dean was at a bar. You were there with the only friend you would ever allow to talk you into clubbing of any kind. She was talking with a guy over at the jukebox, and you watched them for a moment from your seat at the bar. As you turned back, your eyes connected with Dean's, and he smiled. You blushed and looked away, believing that his smile was just a polite gesture when your eyes met, but he was standing behind you a moment later.

"This seat taken," he asked as he sat down next to you.

"It was," you said, "but I guess she lost it when she went to the jukebox."

"Guess so," he said with a smile.

That smile. It was the first time a man smiled at you and it didn't feel skeevy, or fake. The two of you talked for a while before your friend was ready to leave. You said goodbye, but you always remembered his smile.

Six months later, Dean showed up outside your apartment building. You were a bit freaked out until he told you he ran into your friend at the bar the night before. She'd actually given him your building address. Something you severely chewed her out for later.

Yet, here he was, with that smile you never forgot. He asked you out for drinks, and he saw you hesitate to answer.

"You can bring your friend, if you want," he said. "I have a brother. I'll bring him along. I just remember really enjoying talking to you last time we were in town, and I'd like to meet up again."

"Okay. Meet you there at eight?"

"Sounds good," he said.

The four of you sat in a booth. You and Dean sat on one side, while your friend and Dean's brother, Sam, sat on the other. Dean's arm eventually ended up across the top of the seat behind you, and you waited for him to pull some lame move, but he didn't. The two of you talked for hours, you almost forgot that the other two were even there. You found yourself fidgeting, playing with your fingers, moving your hands from your lap, to the table, then back again. Dean noticed and took one of your hands in his, and his thumb gently brushed over your skin. It sent a rush of anxiety through you, but the softness in his eyes relaxed you.

"You know," he said, "me and my brother, we do odd jobs across the country. I've actually looked for work that would bring us through here again so I could see you."

"Really?"

"Yeah. You left way too soon last time."

"The job you found... it's here in town?"

"In the area. About twenty minutes from here, maybe."

"So, you really came here to see me?"

"Of course," he said.

He lifted your hand and held it against his chest. Your eyes were fixed there for a moment before they traveled up and found him smiling. That smile.

That was the first time a man made you feel wanted. But you froze. Long-existing insecurities kicked in and you suddenly felt crushed. You pulled your hand away, and watched as his eyes questioned, then you turned and stared at the table. The next hand you felt was your friend's. She pulled you from the booth as she excused you both, and told Sam and Dean you would be back. You followed her outside and felt a bit of relief as the cool night air filled your lungs.

"What's wrong," she asked. "No. Scratch that. I know what's wrong. Don't push this guy away. He likes you."

"How can you be so sure?"

"How can you not? Sam told me that Dean came back just to see you. He looked for work in the area for months, just so he had an excuse to drive this way again. I saw him holding your hand, looking at you. He's into you... Really into you."

The two of you walked to the corner, away from the noise leaking out of the bar. As she tried to convince you to go back inside and open up, Dean and Sam walked out. Your eyes met, but instead of a smile you saw fear. He started running toward you, then there was blackness.

When you opened your eyes, there was a sharp pain at the back of your head. You were tied to a chair. You looked to your side and saw your friend in the same condition, her head drooping.

And a man. A man with way more teeth than any normal person should have. That was the night you learned that monsters were real. That was the first time someone told you that you really did have a reason to be afraid of the dark. That was also the first time someone saved your life. Dean. He and Sam came charging in, and cut off the monster's head. Dean came to you and freed you from the chair. You stood on shaky legs before Sam called Dean over to your friend, limp in Sam's arms.

That was the first time you openly cried in front of another person.

Your friend was gone, and the town did nothing but remind you of her. So, when Dean asked you to hit the road with them, you took the last piece of advice she gave you, and you agreed.

Another few months went by before Sam jokingly called you Dean's girlfriend. You expected some sort of rebuttal or denial, but Dean just smiled, and winked at you. And then you realized: Dean was your boyfriend. Your first.

One night on the road, you were all exhausted, and Dean pulled into the first motel that didn't look like it had top billing in a horror movie. Sam called for the shower first. While you and Dean were alone, he wrapped his arms around you from behind. He nuzzled your neck and began to kiss along your jaw.

"Dean..." Your voice held a hint of panic, and Dean pulled away.

"What's wrong?" He turned you to face him.

"I..." You hesitated, and looked to the floor.

"You can tell me. Did I get the wrong signals here? 'Cause I kinda thought we had something."

"We do. I just... I have to tell you something."

He put his hands on your arms and rubbed. "What is it?"

"You... You're the first boyfriend I ever had."

Dean surprised you by smiling. "Honestly? I knew."

"You knew?"

"Yeah."

"How?"

"Sam told me."

"Sam? How did Sam--" you watched Dean's eyes sadden, and you knew how Sam knew. Your friend had told him. She knew about Dean looking for you. They had obviously talked about you.

You sat on the edge of the bed and Dean sat next to you, pulling you against him. That night was the first time you opened up completely to anyone.

"Dean... I don't trust people easily."

"I kinda got that impression."

"I have a hard time believing that people give a damn about me." You looked into his eyes and willed yourself not to look away. "I still question sometimes why you're with me."

Dean took your hand and squeezed. "I'm with you because I want to be. I never walked away from a woman before feeling like I had to see her again, but you drew me back."

"But why? I just don't see--"

Dean took your face in his hands and gently pressed his lips to yours. Your instinct was to pull away, but you wrapped your arms around Dean's shoulders instead. He opened his mouth a little, and you felt him probing at your lips with his tongue, but you heard the bathroom door open, and you pulled away. You stood and moved across the room as Sam walked over to the other bed. You expected Dean to be upset, but he just smiled at you.

That was your first kiss.

Kissing. Something else to be self-conscious about, but you must have been a little good at it, because Dean was always stealing kisses. 

Then there was the first time you kissed him. Sam had gone for food and Dean was lying back on top of his bed, resting his eyes. He had his arms crossed over his chest, and his legs crossed at the ankles. You stared at him for a moment before the clenching in your chest drew you to his side. You sat on the edge of the bed, turned slightly to face him. When the bed dipped, he opened his eyes, and you leaned over and pressed your lips to his. His hands moved to your sides as he returned the kiss. He gently pulled you so that you were lying next to him, your hand on his chest, and your leg draped over his, then his hand moved into your hair.

"You are so beautiful," he said.

You heard the Impala rumble to a stop outside, and you sat up. "Do you think, maybe, you can share the bed with me tonight."

"I thought you'd never ask, sweetheart."

That night, you slept on your side, facing away from Sam in the other bed. Dean snuggled up behind you, and you were soon asleep.

A few weeks passed before sharing a bed with Dean turned steamy. You woke one morning to find him staring at you, and your body just took over. You kissed him and he rolled you onto your back as he returned it. Your hands ran down his chest and began to glide up under his shirt. He let out a moan, and you heard a sound from the next bed as Sam must have turned over.

"No way," you heard Sam say. "I knew this was coming."

Dean moved away and put himself between you and Sam, knowing you would be embarrassed. "Chill out, dude. We were just kissing."

"Yeah, right. Not while I'm in the room, you two. That's just gross."

Sam turned back over to go back to sleep. Dean snuggled next to you again.

"You okay," he asked.

"Yeah."

After another half hour of not being able to get back to sleep, you figured you had better tell Dean what was on your mind. You turned in his arms and whispered his name.

"Dean... are you awake?"

He grunted slightly before his eyes fluttered open.

"What's up?"

"I was just thinking... maybe we should get our own room at the next motel."

Now Dean was awake. He sat up a bit, leaning on his elbow. "Are you sure?"

"After this morning? Yeah, I'm sure."

Dean ran the back of a finger over your cheek before kissing you. You gave in for a moment, but pulled back.

"We can't right now."

Dean sighed and rested his forehead against yours. "I know."

He pulled you close, and you were finally able to go back to sleep.

The next motel came two days later, and the fact that it was nicer than usual didn't escape your attention. Your nerves were shot. As badly as you wanted Dean, you were scared. Scared of the intimacy. Scared of being that vulnerable. Scared that you wouldn't measure up to his experience.

Once the two of you were settled, Dean wrapped his arms around you from behind. His lips trailed down your neck, but he stopped.

"You okay, sweetheart?"

"I'm fine."

"No, you're tense." He turned you to face him. "What's wrong?"

"My same old issues."

"Do you trust me," Dean asked.

"How can you ask me that? You know I trust you more than anyone."

"Good, then you know I'll take care of you. If you wanna stop, we stop. I've got you."

Dean leaned down and kissed your lips. You wrapped your arms around his shoulders and let yourself sink into his chest. You felt his hands beneath your ass as he lifted you off your feet, and wrapped your legs around his waist.

He was so strong. It occurred to you then that you loved that about Dean. It was one of the reasons you trusted him with not just your life, but your heart. He made you feel safe and protected.

He carried you to the bed and sat on the edge with you still in his lap. He pulled your shirt over your head, then did the same with his. Your hands went to his chest, and he stared at you as you ran your hands over his body. He eventually reached around your back and undid the clasp of your bra. When he pulled it from you, your arms covered your breasts. Dean smiled and shook his head.

"Hey... I let you fondle me," he said with a grin. "Fair is fair."

You let out a nervous laugh as Dean pulled your arms apart. He licked his lips, then kissed you as his hands covered your breasts and gently squeezed. You whimpered into his mouth, and Dean moaned.

"I've got you," he whispered.

"I know."

He stood again with you in his arms, then turned and laid you on the bed. He undid his jeans, removing them, along with his boxers, the pulled your jeans and underwear from your legs. Your eyes were drawn to his erection, long and hard. Your hand reached out almost on its own, but you drew it back and looked up into Dean's eyes.

He was smiling. "You can touch me if you want."

You got on your knees on the bed, but hesitated. "I don't want to hurt you... Can you show me how you like it?"

Dean took your hand and kissed your palm before he wrapped it around his shaft. He squeezed gently as he moved your hand up and down his length, in long, smooth strokes. Once you had the hang of it, he removed his hand and pulled your face to his for a kiss. Dean moaned, and you smiled against his lips. You had pulled that sound from him... and you liked it. You stroked a little harder and faster, and Dean's hips bucks into your hand as he grunted.

"Shit," he whispered. "Hang on, hang on..."

He pulled your hand away, breathing heavily.

"Did I do something wrong," you asked.

"Hell no. That was good... too good. Can't have me coming before I even get you riled up."

You blushed, and Dean's mouth was suddenly on yours. He climbed over you and carefully pulled you up the bed as you kissed. He lay your head on a pillow and ran a hand through your hair.

"Comfy," he asked.

You nodded. Dean moved to your side and ran his hand down your body as he kissed you. It came to rest on your hip while he licked down to your breasts. When he sucked a nipple into his mouth, your back arched into him. Then you felt his fingers between your legs.

"Dean..." you moaned.

"I've got you, sweetheart." He kissed back up to your lips and looked into your eyes. "You good?"

"Yeah," you said with a nod.

That's when he slipped his finger into you. This felt good. He slowly pumped, in and out, and you moved your hips against his hand. Dean twisted his hand and curled his finger and pressed into a spot that made you shiver, and cry out.

"Found it," he said with a grin.

He ran his finger over the spot a few more times before he removed it, just for a moment, then pushed back in, but this felt fuller. You realized that he had two fingers in you now. Then you remembered how large his dick was, and you began to panic. Dean felt you clench around his fingers, and he stopped moving.

"Hey, I've got you. I'm gonna take care of you. Just relax."

"Dean, it'll hurt..."

"Most likely, but that's why I'm doing this. Getting you ready. You trust me?"

"I trust you."

Dean carefully worked in a third finger and was barely able to move for a moment.

"Relax, sweetheart."

He ran his tongue over one of your nipples and sucked it into his mouth, then slowly pumped his fingers inside of you. When he was finally able to graze over your sweet spot, he withdrew his fingers, and you whimpered.

You watched as he moved between your legs. He rubbed his fingers, covered in your wetness, over his dick, and stroked himself a few times. He placed the placed the tip of his erection at your slick pussy and leaned over to kiss you. While you were lost in the sensation, he slowly slid into you. He stopped as you clenched around him.

"Relax," he whispered against your lips.

You willed your body to calm, and Dean filled you completely with a quick thrust. There was a sharp pain that made you cry out, but Dean kissed your neck and slowly moved inside of you, almost massaging it away.

"You okay, sweetheart?"

"Yeah."

Dean pulled back a little and look into your eyes. He still pumped gently into you.

"Look at me," he said.

You stared back into his eyes as he hit that sweet spot. Your eyes fluttered closed as you moaned, but when you opened them he was still staring down at you, and you locked eyes with him again.

"I love you," he whispered.

Your hands went to his face as you whispered the words back. The first time you ever said those words to a man. And you meant it.

He hit that sweet spot again, and you came undone. He thrust into you harder as you clenched around him, until he too came. He stroked slowly as you both came down, then he moved to your side and held you close. You kissed his neck as he stroked his fingers through your hair.

That was the first time you fell asleep hopeful of what the future would hold for you and Dean.


End file.
